Categories: C-C Bond Formation > Oxygen-containing molecules > α,β-unsaturated compounds >
Synthesis of enones
| Related:
|
 |
 |
 |
 |
 |
 |
Name Reactions
Recent Literature
Starting from readily available aryl iodides and allenes, with formic acid as
the CO source and reductant, good yields of α-branched enones were isolated. The
use of a CO source avoids the manipulation of CO gas.
H.-Q. Geng, L.-C. Wang, C.-Y. Hou, X.-F. Wu,
Org. Lett., 2020, 22, 1160-1163.
A carbonylative Suzuki-Miyaura coupling reaction of lactam-derived vinyl
triflates and alkenylboronic acids afforded 2-(N-methoxycarbonylamino)-1,4-pentadien-3-ones
in good yield.
P. Larini, A. Guarna, E. G. Occhiato, Org. Lett.,
2006,
8, 781-784.
A highly efficient catalytic, intermolecular synthesis of the cyclopentane
skeleton from simple starting products is reported. Allyl halides, alkynes,
and carbon monoxide react under very mild reaction conditions by means of a
substoichiometric amount of iron, acetone, and a catalytic amount of Ni(II)
iodide.
M. L. Nadal, J. Bosch, J. M. Vila, G. Klein, S. Ricart, J. M. Moretó, J.
Am. Chem. Soc.,
2005,
127, 10476-10477.
A new approach to 2-(arylmethyl)aldehydes begins
with a silylformylation reaction of terminal acetylenes with aryl- or
heteroarylsilanes, followed by treatment of the products with TBAF to induce a 1,2-anionotropic
rearrangement of the aryl group.
L. A. Aronica, P. Raffa, A. M. Caporusso, P. Salvadori, J. Org.
Chem., 2003, 5, 9292-9298.
An entrapped Rh catalyst derived by a sol-gel process has been used in a Pauson-Khand reaction under mild conditions. The
catalyst can be reused at least 10 times without losing activity. This
catalytic system is not effective for intermolecular reactions.
K. H. Park, S. U. Song, Y. K. Chung, Tetrahedron Lett., 2003,
44, 2827-2830.
Indanones and 2-cyclopentenones have been successfully prepared in good to
excellent yields by the palladium-catalyzed carbonylative cyclization of
unsaturated aryl iodides and dienyl triflates, iodides, and bromides,
respectively. The mechanism is discussed.
S. V. Gagnier, R. C. Larock, J. Am. Chem. Soc., 2003,
125, 4804-4807.